US 2003/0216573 A1Published application

Method of preparing substituted 4-amino-3-alkylthio-1,2,4-triazine-5-ones

AssigneeBayer MaterialScience AG

InventorDennis E. Jackman

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Abstract

The present invention provides a method of preparing 4-amino-3-alkylthio-1,2,4-triazine-5-ones of the formula (I) 1 wherein R, R1, R2 and R3 are as defined herein, the method comprising reacting in the presence of a base and under at least one condition selected from the presence of at least one inorganic compound selected from inorganic sulfites and inorganic bisulfites, an inert gas purge, and an alternating inert gas blanket and vacuum, a 4-amino-3-mercapto-1,2,4-triazin-5-one of the formula (II) 2 wherein R, R1 and R2 are as defined herein, with an alkylating agent of the formula R3-X, wherein R3 and X are as defined herein and collecting the reaction product.

Claims26

Dependent claims

A method of preparing a 4-amino-3-alkylthio-1,2,4-triazine-5-one of the formula (I)

11
wherein
R represents C3-C8-alkyl, cycloalkyl having 5-10 ring carbon atoms, unsubstituted or C1-C4-alkyl-, C1-C4-alkoxy-, chloro-, or nitro-substituted phenyl, unsubstituted or chloro-substituted phenylalkyl having 1-4 carbons atoms in the alkyl moiety, chlorophenylalkyl having 1-4 carbons atoms in the alkyl moiety, phenylalkenyl having 2-4 carbon atoms in the alkenyl moiety, phenylalkylmercaptoalkyl having 1-4 carbon atoms in the alkylmercapto moiety and 1-4 carbon atoms in the alkyl moiety, furyl, furfuryl, pyranyl, or pyridylmethyl,
R1 and R2 independently represent hydrogen, C1-C4-alkyl, C2-C4-hydroxytrichloro-alkyl, or C2-C5-alkanoyl, and
R3 represents C1-C18-alkyl,
the method comprising:
reacting in the presence of a base and under at least one condition selected from the presence of at least one inorganic compound selected from inorganic sulfites and inorganic bisulfites, an inert gas purge, and an alternating inert gas blanket and vacuum, a 4-amino-3-mercapto-1,2,4-triazin-5-one of the formula (II)
12
wherein R, R1 and R2 are as defined above,
with an alkylating agent of the formula R3-X,
wherein
R3 is as defined above, and
X represents halide, sulfonate, sulfate, phosphate and carbonate;
and
collecting the reaction product.

12 more elements

A method of decreasing color bodies in a 4-amino-6-alkyl-3-alkylthio-1,2,4-triazin-5(4H)-one of the formula (I)

15
wherein
R represents C3-C8-alkyl, cycloalkyl having 5-10 ring carbon atoms, unsubstituted or C1-C4-alkyl-, C1-C4-alkoxy-, chloro-, or nitro-substituted phenyl, unsubstituted or chloro-substituted phenylalkyl having 1-4 carbons atoms in the alkyl moiety, chlorophenylalkyl having 1-4 carbons atoms in the alkyl moiety, phenylalkenyl having 2-4 carbon atoms in the alkenyl moiety, phenylalkylmercaptoalkyl having 1-4 carbon atoms in the alkylmercapto moiety and 1-4 carbon atoms in the alkyl moiety, furyl, furfuryl, pyranyl, or pyridylmethyl,
R1 and R2 independently represent hydrogen, C1-C4-alkyl, C2-C4-hydroxytrichloro-alkyl, or C2-C5-alkanoyl, and
R3 represents C1-C18-alkyl,
the method comprising reacting in the presence of a base and under at least one condition which decreases color bodies in the product selected from the presence of at least one inorganic compound selected from inorganic sulfites and inorganic bisulfites, an inert gas purge, and an alternating inert gas blanket and vacuum, a 4-amino-3-mercapto-1,2,4-triazin-5-one of the formula (II)
16
wherein R, R1 and R2 are as defined above,
with an alkylating agent of the formula R3-X,
wherein
R3 is as defined above, and
X represents halide, sulfonate, sulfate, phosphate and carbonate;
and
collecting the reaction product.

11 more elements

Dependencies are inferred from the claim text.